Activation of functional arylzincs prepared from aryl iodides and highly enantioselective addition to aldehydes

被引：41

作者：

DeBerardinis, Albert M. ^{[1
]}

Turlington, Mark ^{[1
]}

Pu, Lin ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 13期

关键词：

D O I：

10.1021/ol8008478

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An easily available chiral ligand (S)-1 is found to activate the nucleophilic reaction of the arylzincs prepared in situ from the reaction of aryl iodides with Et2Zn. Both high yields and high enantioselectivity (up to >99% ee) for the reaction of these arylzincs with a variety of aldehydes are obtained. The mild reaction conditions and the good functional group tolerance make this catalytic asymmetric process synthetically useful.

引用

页码：2709 / 2712

页数：4

共 50 条

[31] New and improved ligands for highly enantioselective catalytic diphenylzinc additions to aryl aldehydes
Huang, WS
Pu, L
TETRAHEDRON LETTERS, 2000, 41 (02) : 145 - 149
[32] Highly effective and recyclable dendritic ligands for the enantioselective aryl transfer reactions to aldehydes
Liu, XY
Wu, XY
Chai, Z
Wu, YY
Zhao, G
Zhu, SZ
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (18): : 7432 - 7435
[33] Chiral 1,3-oxazolidines as the ligands for the enantioselective addition of diethylzinc to aryl aldehydes
Prasad, KRK
Joshi, NN
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2003, 42 (01): : 150 - 153
[34] CHIRAL PIPERAZINE AS A NEW CHIRAL CATALYST FOR THE ENANTIOSELECTIVE ADDITION OF DIALKYL ZINCS TO ARYL ALDEHYDES
SOAI, K
NIWA, S
YAMADA, Y
INOUE, H
TETRAHEDRON LETTERS, 1987, 28 (41) : 4841 - 4842
[35] Enantioselective addition of diethylzinc to aryl aldehydes catalyzed by novel chiral imino alcohol ligands
P. Salehi
M. Dabiri
G. Kozehgary
Journal of the Iranian Chemical Society, 2010, 7 : 100 - 106
[36] Enantioselective Addition of Diethylzinc to Aryl Aldehydes Catalyzed by Novel Chiral Imino Alcohol Ligands
Salehi, P.
Dabiri, M.
Kozehgary, G.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2010, 7 (01) : 100 - 106
[37] Highly enantioselective addition of arylzinc reagents to aldehydes promoted by chiral aziridine alcohols
Wujkowska, Zuzanna
Jarzynski, Szymon
Pieczonka, Adam M.
Lesniak, Stanislaw
Rachwalski, Michal
TETRAHEDRON-ASYMMETRY, 2016, 27 (24) : 1238 - 1244
[38] New β-amino thiols as efficient catalysts for highly enantioselective alkenylzinc addition to aldehydes
Tseng, SL
Yang, TK
TETRAHEDRON-ASYMMETRY, 2005, 16 (04) : 773 - 782
[39] Highly enantioselective diethylzinc addition to aldehydes catalyzed by D-glucosamine derivatives
Bauer, T
Tarasiuk, J
Pasniczek, K
TETRAHEDRON-ASYMMETRY, 2002, 13 (01) : 77 - 82
[40] Highly enantioselective conjugate addition of aldehydes to nitroolefins catalyzed by chiral bifunctional sulfamides
Zhang, Xue-jing
Liu, Sheng-ping
Li, Xue-ming
Yan, Ming
Chan, Albert S. C.
CHEMICAL COMMUNICATIONS, 2009, (07) : 833 - 835

← 1 2 3 4 5 →